mescaline

 

Mescaline
Systematic (IUPAC) name
3,4,5-trimethoxy-phenethylamine or 2-(3,4,5-trimethoxyphenyl) ethanamine
Identifiers
CAS number	54-04-6
ATC code	?
PubChem	?
Chemical data
Formula	C11H17NO3
Mol. mass	211.26 g/mol
SMILES	search in eMolecules, PubChem
Physical data
Melt. point	183–186 °C (361–367 °F) (Sulfate dihydrate)
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	X(AU) X(US)
Legal status	Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US)
Routes	Oral, Intravenous

Mescaline (3,4,5-trimethoxyphenethylamine) is a psychedelic alkaloid of the phenethylamine class. It is mainly used as; a recreational drug, an entheogen, and a tool in use to supplement various types of practices for transcendence, including in meditation, psychonautics, and illegal psychedelic psychotherapy, whether self administered or not.

It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi) and the Peruvian Torch cactus (Echinopsis peruviana), and in a number of other members of the Cactaceae. It is also found in small amounts in certain members of the Fabaceae (bean family), including Acacia berlandieri.^[1] Mescaline was first isolated and identified in 1897 by the German Arthur Heffter and first synthesized in 1919 by Ernst Späth.

Usage and history

The use of peyote in Native American religious ceremonies has been noted since the earliest European contact, notably by the Huichols in Mexico, but other cacti such as the San Pedro have been used in different regions, from Peru to Ecuador.

Dosage and effects

In traditional peyote preparations, the top of the cactus is cut from the roots, and dried to make disk-shaped buttons. It is chewed to produce its effect or soaked in water for an intoxicating drink. However, the taste of the cactus is bitter, so users will often grind it into a powder and fill them in capsules to avoid having to taste it. The effective human dosage is 300–500 milligrams of pure mescaline, with the effects lasting for up to 12 hours. Hallucinations occur at 300–600 mg, which is the equivalent to approximately 20 mescal buttons. Users typically experience visual hallucinations and radically altered states of consciousness, often experienced as pleasurable and illuminating but occasionally is accompanied by feelings of anxiety or revulsion. Like most psychedelic hallucinogens, mescaline is not physically addictive. Mescaline-containing cacti can induce severe vomiting and nausea, which adds an important part to traditional Native-American or Shaman ceremonies as it is considered cleansing.

Mode of action

It is speculated that mescaline, along with LSD, psilocybin, 5-Meo-DMT and tryptamine bind to the 5-HT receptors, specifically the 5-HT2A receptor which is a G protein-coupled receptor. Binding to the receptor active site in the neuron causes the G protein to dissociate and become activated with GTP. This released G protein complex stimulates various physical and chemical changes within the cell. It can directly alter the membrane sensitivity to ion transport via conformational changes, stimulate the release of ions from cellular storage, and also stimulate transcription and editing of the primary transcript with the end result of increased ionic activity—all of these methods leading to a change in the neuronal potential. In certain neural cells, this stimulation is inhibitory in action (resulting in the changed perception of edges) while in others it is excitatory, resulting in the positive symptoms of the "hallucination" or "vision".

Pharmacokinetics

Although the ED₅₀ is variable with dosage and individual, the LD₅₀ has been measured in various animals and is reported as follows:

• Crystals: 212 mg/kg i.p. (mice)

• Crystals: 132 mg/kg i.p. (rats)

• Crystals: 328 mg/kg i.p. (guinea pigs)

It is reported that mescaline is 1000-3000 times less potent than LSD, and 30 times less potent than psilocybin. About half the initial dosage is excreted after 6 hours, but some studies suggest that it is not metabolized at all before excretion.

Slow tolerance builds with repeated usage, and it is suggested that a cross tolerance can be developed with LSD.

Legal status

In the US it was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act. It was prohibited internationally by the 1971 Convention on Psychotropic Substances[1] and is categorized as a Schedule I hallucinogen by the CSA. Mescaline is only legal for certain natives (such as those involved in the Native American Church). Penalties for manufacture or sale can be as high as five years in jail and a fine of $15,000, with a penalty of up to one year and fine of $5000 for possession.

"Mescaline is a controlled substance, U.S. code of Federal Regulations, title 21 part 1308.11(1987)."^[2]

Chemistry

A common synthetic approach starts from 3,4,5-trimethoxybenzaldehyde. The chemical make-up is C₁₁H₁₇NO₃ (PiHKAL entry). It is also synthesized from syringaldehyde, vanillin, and gallic acid. 3,4,5-trimethoxynitrostyrene can be reduced to mescaline using catalytic hydrogenation.

Effects and side effects

One or more of the following effects may or may not accompany any individual experience with mescaline.

• Uncontrollable laughter
• Open and closed eye visualizations
• Dream-like scenarios
• Euphoria
• Psychedelic experience
• Pupil dilation
• Sensations of warm and cold
• Dizziness
• Vomiting
• Tachycardia
• Diarrhea
• Headaches
• Anxiety

Analogs

Mescaline has a number of analogs, featuring the methoxy groups altered to include thio groups or to be extended. Examples include, but are not limited to, isomescaline, thiomescaline, escaline, thioescaline, proscaline, isoproscaline, buscaline, thiobuscaline, thioisomescaline, phenescaline, symbescaline, asymbescaline, thioasymbescaline, allylescaline, methallylescaline, metaescaline, and thiometaescaline.

See also

• The Doors of Perception
• Project MKULTRA
• PiHKAL
• Psychoactive drug
• List of notable people who have taken psychedelic drugs

References

Notes

General References

• http://www.drugs.com/dict/mescaline.html
• http://www.streetdrugs.org/mescaline.htm
• http://www.mescaline.org/exp/index.htm
• http://www.drugeducation.net/mescaline.htm
• http://www.drugtext.org/library/books/recreationaldrugs/mescaline.htm
• http://www.mescaline.com/synth/
• http://www.narconon.ca/mescaline.htm
• http://www.goaskalice.columbia.edu/2323.html
• http://www.lycos.com/info/mescaline.html
• http://library.thinkquest.org/C005038/mescaline.htm
• http://leda.lycaeum.org/?ID=12
• http://www.dummies.com/WileyCDA/DummiesArticle/id-2836.html
• Rostock, D. T. (2003, Spring). Pharmacological constituents of mescaline and salvinorin-A. University of Idaho, Department of Psychology.
• Nichols; Sanders-Bush, E. (2001). "Serotonin receptor signaling and hallucinogenic drug action". The Heffter Review of Psychedelic Research 2: 73-79. 
• Rostock, D. T. (2003). Pharmacological constituents of mescaline and salvinorin-A. University of Idaho, Department of Psychology. 

Cultural References

• In the movie Fear and Loathing in Las Vegas (film), the main characters do mescaline.

External links

• Mescaline at Erowid
• PiHKAL entry
• Mescaline: The Chemistry and Pharmacology of its Analogs Essay by Alexander Shulgin

Categorization

Psychedelic phenethylamines

Aleph • 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA-2 • DOB • DOC • DOET • DOI • DOM • DON • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • Isoproscaline • Lophophine • MDA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Proscaline • TMA

Drugs from PiHKAL

AEM · AL · Aleph · Aleph-2 · Aleph-4 · Aleph-6 · Aleph-7 · Ariadne · Asymbescaline · Buscaline · Beatrice · Bis-TOM · BOB · BOD · BOH · BOHD · BOM · 4-Bromo-3,5-dimethoxyamphetamine · 2-Bromo-4,5-methylenedioxyamphetamine · 2C-B · 3C-BZ · 2C-C · 2C-D · 2C-E · 3C-E · 2C-F · 2C-G · 2C-G-3 · 2C-G-4 · 2C-G-5 · 2C-G-N · 2C-H · 2C-I · 2C-N · 2C-O · 2C-O-4 · 2C-P · CPM · 2C-SE · 2C-T · 2C-T-2 · 2C-T-4 · psi-2C-T-4 · 2C-T-7 · 2C-T-8 · 2C-T-9 · 2C-T-13 · 2C-T-15 · 2C-T-17 · 2C-T-21 · 4-D · beta-D · DESOXY · 2,4-DMA · 2,5-DMA · 3,4-DMA · DMCPA · DME · DMMDA · DMMDA-2 · DMPEA · DOAM · DOB · DOBU · DOC · DOEF · DOET · DOI · DOM · psi-DOM · DON · DOPR · Escaline · EEE · EEM · EME · EMM · Ethyl-J (EBDB) · Ethyl-K · F-2 · F-22 · Flea · 3C-G-3 · 3C-G-4 · 3C-G-5 · 3C-G-N · Ganesha · HOT-2 · HOT-7 · HOT-17 · IDNNA · Isomescaline · Isoproscaline · Iris · J (BDB) · Lophophine · Mescaline · 4-MA · Madam-6 · Methallylescaline · MDA · MDAL · MDBU · MDBZ · MDCPM · MDDM · MDE · MDHOET · MDIP · MDMA · MDMC (EDMA) · MDMEO · MDMEOET · MDMP · MDOH · MDPEA · MDPH · MDPL · MDPR · Metaescaline · MEDA · MEE · MEM · MEPEA · Meta-DOB · Meta-DOT · Methyl-DMA · Methyl-DOB · Methyl-J (MBDB) · Methyl-K · Methyl-MA (PMMA) · Methyl-MMDA-2 · MMDA · MMDA-2 · MMDA-3a · MMDA-3b · MME · Metaproscaline · MPM · Ortho-DOT · Proscaline · Phenescaline · Phenethylamine · Propynyl · Symbescaline · 2,3,4,5-Tetramethoxyamphetamine · 3-TASB · 4-TASB · 5-TASB · Thiobuscaline · 3-TE · 4-TE · 3-TIM · 4-TIM · 5-TIM · 3-TM · 4-TM · TMA · TMA-2 · TMA-3 · TMA-4 · TMA-5 · TMA-6 · 3-TME · 4-TME · 5-TME · 2T-MMDA-3a · 4T-MMDA-2 · 2-TOET · 5-TOET · 2-TOM · 5-TOM · TOMSO · Thioproscaline · Trisescaline · 3-TSB · 4-TSB · 3-T-Trisescaline · 4-T-Trisescaline

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